# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02446AndreaGuerrero
_database_code_depnum_ccdc_archive 'CCDC 1880124'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;X-Ray Diffraction Laboratory, Servicio Interdepartamental de Investigaci?n, Universidad Aut?noma de 
Spain
;
_audit_update_record             
;
2018-11-20 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JA-58-cristal1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25.50 H25 B Br3 Cl F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         683.46
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'-x, -y, z+1/2'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.0614(4)
_cell_length_b                   12.0614(4)
_cell_length_c                   37.3048(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5427.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9243
_cell_measurement_theta_min      2.3524
_cell_measurement_theta_max      19.7756
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear intense orange-red'
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.182
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2696

_exptl_absorpt_coefficient_mu    4.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_T_max  0.49

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            92650
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44

_refine_special_details          
;
;

_reflns_number_total             4987
_reflns_number_gt                3915
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1720
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²+9.9164P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.774
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 1.1224(9) 0.3178(8) 0.0612(3) 0.041(2) Uani d . . . 1 . .
Br Br1 0.56843(18) -0.0098(2) -0.00152(6) 0.1448(9) Uani d . . . 1 . .
Br Br2 0.82287(15) 0.04500(16) -0.00207(4) 0.1049(6) Uani d . . . 1 . .
Br Br3 0.94756(11) -0.25242(9) 0.11183(3) 0.0703(4) Uani d . . . 1 . .
C C1 1.2204(8) 0.1381(8) 0.0422(2) 0.045(2) Uani d . . . 1 . .
H H1 1.272 0.1715 0.0272 0.054 Uiso calc U . R 1 . .
C C2 1.2069(8) 0.0250(8) 0.0462(2) 0.048(2) Uani d . . . 1 . .
H H2 1.2466 -0.0298 0.0343 0.057 Uiso calc U . R 1 . .
C C3 1.1244(8) 0.0082(7) 0.0710(2) 0.042(2) Uani d . . . 1 . .
H H3 1.0984 -0.0598 0.0792 0.05 Uiso calc U . R 1 . .
C C4 1.0867(7) 0.1145(7) 0.0816(2) 0.0337(17) Uani d . . . 1 . .
C C5 1.0080(6) 0.1478(6) 0.10656(19) 0.0302(16) Uani d . . . 1 . .
C C6 0.9886(7) 0.2625(6) 0.1127(2) 0.0337(17) Uani d . . . 1 . .
C C7 0.9179(7) 0.3174(7) 0.1365(2) 0.041(2) Uani d . . . 1 . .
H H7 0.8703 0.2848 0.153 0.05 Uiso calc U . R 1 . .
C C8 0.9325(9) 0.4300(7) 0.1306(3) 0.053(2) Uani d . . . 1 . .
H H8 0.8975 0.4873 0.1429 0.064 Uiso calc U . R 1 . .
C C9 1.0092(8) 0.4411(7) 0.1031(2) 0.045(2) Uani d . . . 1 . .
H H9 1.0324 0.5083 0.0934 0.054 Uiso calc U . R 1 . .
C C10 0.9348(7) 0.0655(6) 0.12641(19) 0.0324(16) Uani d . . . 1 . .
H H10 0.8877 0.11 0.1423 0.039 Uiso calc U . R 1 . .
C C11 1.0019(7) -0.0117(6) 0.1511(2) 0.0339(17) Uani d . . . 1 . .
H H11 1.0547 -0.0525 0.1362 0.041 Uiso calc U . R 1 . .
C C12 0.9274(8) -0.0961(7) 0.1695(2) 0.045(2) Uani d . . . 1 . .
H H12A 0.8815 -0.0581 0.1869 0.054 Uiso calc U . R 1 . .
H H12B 0.9734 -0.1487 0.1823 0.054 Uiso calc U . R 1 . .
C C13 0.8525(8) -0.1595(7) 0.1436(2) 0.049(2) Uani d . . . 1 . .
C C14 0.7866(8) -0.0813(7) 0.1198(2) 0.045(2) Uani d . . . 1 . .
H H14A 0.7466 -0.125 0.1022 0.053 Uiso calc U . R 1 . .
H H14B 0.7322 -0.0433 0.1345 0.053 Uiso calc U . R 1 . .
C C15 0.8544(7) 0.0044(7) 0.1003(2) 0.0350(17) Uani d . . . 1 . .
H H15 0.8988 -0.0333 0.0819 0.042 Uiso calc U . R 1 . .
C C16 0.7817(9) 0.0923(9) 0.0817(3) 0.056(3) Uani d . . . 1 . .
H H16A 0.7498 0.1396 0.1001 0.067 Uiso calc U . R 1 . .
H H16B 0.829 0.1383 0.0669 0.067 Uiso calc U . R 1 . .
C C17 0.6898(8) 0.0481(10) 0.0590(3) 0.058(3) Uani d . . . 1 . .
H H17 0.6234 0.0327 0.0707 0.07 Uiso calc U . R 1 . .
C C18 0.6920(9) 0.0292(9) 0.0254(3) 0.061(3) Uani d . . . 1 . .
C C19 1.0685(8) 0.0547(7) 0.1787(2) 0.042(2) Uani d . . . 1 . .
C C20 1.1843(8) 0.0546(9) 0.1770(3) 0.056(2) Uani d . . . 1 . .
H H20 1.2211 0.0157 0.159 0.067 Uiso calc U . R 1 . .
C C21 1.2425(12) 0.1125(12) 0.2021(4) 0.081(4) Uani d . . . 1 . .
H H21 1.3195 0.1111 0.2014 0.097 Uiso calc U . R 1 . .
C C22 1.1903(15) 0.1731(12) 0.2286(4) 0.088(5) Uani d . . . 1 . .
H H22 1.2316 0.2125 0.2454 0.105 Uiso calc U . R 1 . .
C C23 1.0792(14) 0.1745(10) 0.2298(3) 0.077(4) Uani d . . . 1 . .
H H23 1.0433 0.2154 0.2475 0.093 Uiso calc U . R 1 . .
C C24 1.0167(10) 0.1150(9) 0.2048(2) 0.056(3) Uani d . . . 1 . .
H H24 0.9396 0.1164 0.206 0.067 Uiso calc U . R 1 . .
C C25 0.7765(11) -0.2395(10) 0.1638(3) 0.082(4) Uani d . . . 1 . .
H H25A 0.731 -0.1986 0.1803 0.122 Uiso calc U . R 1 . .
H H25B 0.8207 -0.292 0.1768 0.122 Uiso calc U . R 1 . .
H H25C 0.7302 -0.2781 0.147 0.122 Uiso calc U . R 1 . .
C C26 0.6585(12) 0.6585(12) 0 0.096(6) Uani d T P S 1 . .
H H26A 0.6707 0.5795 0.0026 0.115 Uiso calc U P R 0.5 . .
H H26B 0.5795 0.6707 -0.0026 0.115 Uiso calc U P R 0.5 . .
Cl Cl1 0.7042(5) 0.7250(4) 0.03811(11) 0.1326(19) Uani d . . . 1 . .
F F1 1.0717(7) 0.3410(5) 0.02918(14) 0.079(2) Uani d . . . 1 . .
F F2 1.2198(5) 0.3781(5) 0.06410(19) 0.077(2) Uani d . . . 1 . .
N N1 1.1495(6) 0.1918(5) 0.06281(16) 0.0335(15) Uani d . . . 1 . .
N N2 1.0449(6) 0.3416(5) 0.09247(17) 0.0335(14) Uani d . . . 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.370(12) ?
B1 F2 . 1.386(12) ?
B1 N2 . 1.524(12) ?
B1 N1 . 1.555(11) ?
Br1 C18 . 1.858(10) ?
Br2 C18 . 1.892(12) ?
Br3 C13 . 1.994(10) ?
C1 N1 . 1.319(11) ?
C1 C2 . 1.382(14) ?
C1 H1 . 0.93 ?
C2 C3 . 1.372(13) ?
C2 H2 . 0.93 ?
C3 C4 . 1.416(12) ?
C3 H3 . 0.93 ?
C4 C5 . 1.389(11) ?
C4 N1 . 1.391(11) ?
C5 C6 . 1.421(11) ?
C5 C10 . 1.520(11) ?
C6 N2 . 1.392(10) ?
C6 C7 . 1.399(12) ?
C7 C8 . 1.386(12) ?
C7 H7 . 0.93 ?
C8 C9 . 1.390(14) ?
C8 H8 . 0.93 ?
C9 N2 . 1.335(11) ?
C9 H9 . 0.93 ?
C10 C11 . 1.540(11) ?
C10 C15 . 1.561(11) ?
C10 H10 . 0.98 ?
C11 C12 . 1.520(11) ?
C11 C19 . 1.531(11) ?
C11 H11 . 0.98 ?
C12 C13 . 1.527(13) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.520(13) ?
C13 C25 . 1.529(13) ?
C14 C15 . 1.506(12) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.540(13) ?
C15 H15 . 0.98 ?
C16 C17 . 1.495(14) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.274(15) ?
C17 H17 . 0.93 ?
C19 C24 . 1.369(14) ?
C19 C20 . 1.398(13) ?
C20 C21 . 1.364(16) ?
C20 H20 . 0.93 ?
C21 C22 . 1.38(2) ?
C21 H21 . 0.93 ?
C22 C23 . 1.34(2) ?
C22 H22 . 0.93 ?
C23 C24 . 1.397(16) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C26 Cl1 7 1.722(12) ?
C26 Cl1 . 1.722(12) ?
C26 H26A . 0.97 ?
C26 H26B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 109.9(8) ?
F1 B1 N2 . . 110.8(8) ?
F2 B1 N2 . . 111.1(8) ?
F1 B1 N1 . . 109.2(7) ?
F2 B1 N1 . . 109.4(8) ?
N2 B1 N1 . . 106.4(7) ?
N1 C1 C2 . . 110.2(8) ?
N1 C1 H1 . . 124.9 ?
C2 C1 H1 . . 124.9 ?
C3 C2 C1 . . 107.7(8) ?
C3 C2 H2 . . 126.1 ?
C1 C2 H2 . . 126.1 ?
C2 C3 C4 . . 106.6(8) ?
C2 C3 H3 . . 126.7 ?
C4 C3 H3 . . 126.7 ?
C5 C4 N1 . . 121.0(7) ?
C5 C4 C3 . . 131.9(8) ?
N1 C4 C3 . . 107.0(7) ?
C4 C5 C6 . . 120.1(7) ?
C4 C5 C10 . . 122.3(7) ?
C6 C5 C10 . . 117.5(7) ?
N2 C6 C7 . . 108.4(7) ?
N2 C6 C5 . . 120.0(7) ?
C7 C6 C5 . . 131.6(8) ?
C8 C7 C6 . . 106.7(8) ?
C8 C7 H7 . . 126.7 ?
C6 C7 H7 . . 126.7 ?
C7 C8 C9 . . 107.2(8) ?
C7 C8 H8 . . 126.4 ?
C9 C8 H8 . . 126.4 ?
N2 C9 C8 . . 110.3(8) ?
N2 C9 H9 . . 124.8 ?
C8 C9 H9 . . 124.8 ?
C5 C10 C11 . . 112.4(7) ?
C5 C10 C15 . . 111.4(6) ?
C11 C10 C15 . . 114.5(6) ?
C5 C10 H10 . . 105.9 ?
C11 C10 H10 . . 105.9 ?
C15 C10 H10 . . 105.9 ?
C12 C11 C19 . . 111.0(6) ?
C12 C11 C10 . . 111.4(7) ?
C19 C11 C10 . . 111.2(6) ?
C12 C11 H11 . . 107.7 ?
C19 C11 H11 . . 107.7 ?
C10 C11 H11 . . 107.7 ?
C11 C12 C13 . . 113.6(7) ?
C11 C12 H12A . . 108.8 ?
C13 C12 H12A . . 108.8 ?
C11 C12 H12B . . 108.8 ?
C13 C12 H12B . . 108.8 ?
H12A C12 H12B . . 107.7 ?
C14 C13 C12 . . 111.5(7) ?
C14 C13 C25 . . 111.5(9) ?
C12 C13 C25 . . 111.1(8) ?
C14 C13 Br3 . . 107.5(6) ?
C12 C13 Br3 . . 108.5(7) ?
C25 C13 Br3 . . 106.4(7) ?
C15 C14 C13 . . 115.2(7) ?
C15 C14 H14A . . 108.5 ?
C13 C14 H14A . . 108.5 ?
C15 C14 H14B . . 108.5 ?
C13 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C14 C15 C16 . . 112.4(7) ?
C14 C15 C10 . . 111.1(6) ?
C16 C15 C10 . . 108.0(7) ?
C14 C15 H15 . . 108.5 ?
C16 C15 H15 . . 108.5 ?
C10 C15 H15 . . 108.5 ?
C17 C16 C15 . . 115.6(9) ?
C17 C16 H16A . . 108.4 ?
C15 C16 H16A . . 108.4 ?
C17 C16 H16B . . 108.4 ?
C15 C16 H16B . . 108.4 ?
H16A C16 H16B . . 107.4 ?
C18 C17 C16 . . 127.3(10) ?
C18 C17 H17 . . 116.3 ?
C16 C17 H17 . . 116.3 ?
C17 C18 Br1 . . 124.1(9) ?
C17 C18 Br2 . . 122.2(8) ?
Br1 C18 Br2 . . 113.7(5) ?
C24 C19 C20 . . 119.3(9) ?
C24 C19 C11 . . 121.1(9) ?
C20 C19 C11 . . 119.6(9) ?
C21 C20 C19 . . 118.8(12) ?
C21 C20 H20 . . 120.6 ?
C19 C20 H20 . . 120.6 ?
C20 C21 C22 . . 121.9(13) ?
C20 C21 H21 . . 119.0 ?
C22 C21 H21 . . 119.0 ?
C23 C22 C21 . . 119.1(11) ?
C23 C22 H22 . . 120.4 ?
C21 C22 H22 . . 120.4 ?
C22 C23 C24 . . 120.7(13) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C19 C24 C23 . . 120.1(11) ?
C19 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C13 C25 H25A . . 109.5 ?
C13 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C13 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
Cl1 C26 Cl1 7 . 112.6(12) ?
Cl1 C26 H26A 7 . 109.1 ?
Cl1 C26 H26A . . 109.1 ?
Cl1 C26 H26B 7 . 109.1 ?
Cl1 C26 H26B . . 109.1 ?
H26A C26 H26B . . 107.8 ?
C1 N1 C4 . . 108.4(7) ?
C1 N1 B1 . . 126.4(7) ?
C4 N1 B1 . . 124.1(7) ?
C9 N2 C6 . . 107.4(7) ?
C9 N2 B1 . . 126.5(7) ?
C6 N2 B1 . . 125.8(7) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -0.9(11) ?
C1 C2 C3 C4 . . . . 0.9(10) ?
C2 C3 C4 C5 . . . . -177.5(8) ?
C2 C3 C4 N1 . . . . -0.6(9) ?
N1 C4 C5 C6 . . . . 1.5(11) ?
C3 C4 C5 C6 . . . . 178.1(8) ?
N1 C4 C5 C10 . . . . 177.5(7) ?
C3 C4 C5 C10 . . . . -6.0(13) ?
C4 C5 C6 N2 . . . . 2.9(11) ?
C10 C5 C6 N2 . . . . -173.2(7) ?
C4 C5 C6 C7 . . . . -178.0(8) ?
C10 C5 C6 C7 . . . . 5.9(13) ?
N2 C6 C7 C8 . . . . -0.4(10) ?
C5 C6 C7 C8 . . . . -179.6(9) ?
C6 C7 C8 C9 . . . . 1.3(11) ?
C7 C8 C9 N2 . . . . -1.9(11) ?
C4 C5 C10 C11 . . . . 64.5(9) ?
C6 C5 C10 C11 . . . . -119.4(7) ?
C4 C5 C10 C15 . . . . -65.5(9) ?
C6 C5 C10 C15 . . . . 110.5(8) ?
C5 C10 C11 C12 . . . . -177.7(6) ?
C15 C10 C11 C12 . . . . -49.2(9) ?
C5 C10 C11 C19 . . . . 58.0(8) ?
C15 C10 C11 C19 . . . . -173.6(7) ?
C19 C11 C12 C13 . . . . 175.9(8) ?
C10 C11 C12 C13 . . . . 51.4(10) ?
C11 C12 C13 C14 . . . . -52.6(11) ?
C11 C12 C13 C25 . . . . -177.7(9) ?
C11 C12 C13 Br3 . . . . 65.7(9) ?
C12 C13 C14 C15 . . . . 52.2(10) ?
C25 C13 C14 C15 . . . . 177.1(9) ?
Br3 C13 C14 C15 . . . . -66.6(8) ?
C13 C14 C15 C16 . . . . -170.5(8) ?
C13 C14 C15 C10 . . . . -49.4(10) ?
C5 C10 C15 C14 . . . . 176.9(7) ?
C11 C10 C15 C14 . . . . 48.0(9) ?
C5 C10 C15 C16 . . . . -59.5(9) ?
C11 C10 C15 C16 . . . . 171.6(7) ?
C14 C15 C16 C17 . . . . -49.9(11) ?
C10 C15 C16 C17 . . . . -172.7(8) ?
C15 C16 C17 C18 . . . . -93.5(14) ?
C16 C17 C18 Br1 . . . . -172.3(8) ?
C16 C17 C18 Br2 . . . . 4.8(17) ?
C12 C11 C19 C24 . . . . -58.2(10) ?
C10 C11 C19 C24 . . . . 66.3(10) ?
C12 C11 C19 C20 . . . . 122.2(9) ?
C10 C11 C19 C20 . . . . -113.2(9) ?
C24 C19 C20 C21 . . . . 1.6(14) ?
C11 C19 C20 C21 . . . . -178.8(9) ?
C19 C20 C21 C22 . . . . -1.5(17) ?
C20 C21 C22 C23 . . . . 0.5(19) ?
C21 C22 C23 C24 . . . . 0.3(19) ?
C20 C19 C24 C23 . . . . -0.8(14) ?
C11 C19 C24 C23 . . . . 179.6(9) ?
C22 C23 C24 C19 . . . . -0.2(17) ?
C2 C1 N1 C4 . . . . 0.6(10) ?
C2 C1 N1 B1 . . . . -168.0(8) ?
C5 C4 N1 C1 . . . . 177.4(7) ?
C3 C4 N1 C1 . . . . 0.0(9) ?
C5 C4 N1 B1 . . . . -13.8(11) ?
C3 C4 N1 B1 . . . . 168.8(8) ?
F1 B1 N1 C1 . . . . 65.8(12) ?
F2 B1 N1 C1 . . . . -54.4(11) ?
N2 B1 N1 C1 . . . . -174.6(8) ?
F1 B1 N1 C4 . . . . -101.0(9) ?
F2 B1 N1 C4 . . . . 138.8(8) ?
N2 B1 N1 C4 . . . . 18.6(11) ?
C8 C9 N2 C6 . . . . 1.6(10) ?
C8 C9 N2 B1 . . . . 175.1(8) ?
C7 C6 N2 C9 . . . . -0.8(9) ?
C5 C6 N2 C9 . . . . 178.5(7) ?
C7 C6 N2 B1 . . . . -174.3(8) ?
C5 C6 N2 B1 . . . . 5.0(12) ?
F1 B1 N2 C9 . . . . -68.1(11) ?
F2 B1 N2 C9 . . . . 54.3(12) ?
N1 B1 N2 C9 . . . . 173.4(8) ?
F1 B1 N2 C6 . . . . 104.2(9) ?
F2 B1 N2 C6 . . . . -133.3(8) ?
N1 B1 N2 C6 . . . . -14.3(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 F1 7_645 0.93 2.56 3.139(10) 120.6 ?
C9 H9 Br3 1_565 0.93 3.14 3.785(8) 128.2 ?

